L-Idose, 6-nitro-6-desoxy

J. M. Grosheintz and H. O. L. Fischer, Synthesis of 6-nitro-6-desoxy-D-glucose and 6-nitro-6-desoxy-L-idose, J. Am. Chem. Soc., 70 (1948) 1476-1479. 

These isomeric acetonated nitrodesoxy sugars could not be separated by fractional crystallization but a selective re-acetonation of the mixture gave mainly the di-isopropylidene derivative of the nitrodesoxy-L-idose, which then could be separated readily from the unchanged mono-iso-propylidene nitrodesoxy-D-glucose. Hydrolysis of the isopropylidene substituents with dilute acid then gave, respectively, 6-nitro-6-desoxy-L-idose and 6-nitro-6-desoxy-D-glucose. 

Thus, either of the nitrodesoxy sugars may be expected to give a mixture containing any of eight possible diastereoisomeric nitrodesoxy inositols. Actually, three individual nitrodesoxy inositols were isolated, and all three were obtained from the cyclization of either 6-nitro-6-desoxy-D-glucose or 6-nitro-6-desoxy-L-idose. 

N 6.70%. A mixt of nitrodesoxyinositols was obtd by cyclization of 6-ftitro-o-desoxy-D-glucose, of 6-nitro-6-desoxy-L-idose or of an equimolar mixt of the two using very small amts of alkali Nitrodesoxyinositol l, crysts (from dioxane), mp 147-48° insol in acet... 

---